Chapter 3

We went inside and dressed for an earlier dinner. Jess skillfully rolled a joint. She had become a substantial marijuana enthusiast since our previous stint together. She favored edibles, but smoked frequently, too. I thought it was sexy to see her puff on a joint or a bowl. When she was stoned, it made her more submissive than usual. Perhaps paradoxically, she liked it extremely rough while high.

Sitting on our deck, we passed the joint back and forth until it was finished. Jess had a dreamy, relaxed look on her face. She had changed into a white halter dress that was long but had dramatic slits up both thighs. Her nipples poked through the tight top, and the billowy fabric frequently bunched between her ass cheeks.

"Let's go eat and capitalize on these munchies," she said slowly. "And then you're going to come back here, take out my butt plug, and absolutely punish my asshole."

I raised my eyebrows. The high from the weed was pleasant and mellow. "Oh really?" I said.

"I need a really hard anal fuck," she said. "I've been a bad girl, and I need you to punish me accordingly."

"Have you been a bad girl?" I said with a hint of surprise.

"I'll tell you at dinner," she said. "I've been waiting until our getaway to talk about it."

The meal was superb. There always was something magical about eating seafood that had been caught yards from where you sat. The wine was expensive but good, and it was worth the island markup.

"So I set up a sugarbaby profile," Jess blurted out after we had finished a bottle of wine.

I looked at her with a surprised smile. "You are feeling frisky," I said.

"I haven't done anything yet," she said quickly. "I mean, I haven't messaged anyone. Just set it up. And my face isn't in the pictures or anything. I just." She stopped short.

"Is there something more I can do for you?" I asked.

"No! Not at all!" she said. "You're perfect. You know me." She had a sheepish look on her face.

"You know, now that I think about it," I said, "you haven't had any fun in almost two years. And you've let me have a good bit of fun. Kat, Rita, Gloria..."

"So, technically, I may have not been totally forthcoming about my year of celibacy," she said.

I raised my eyebrows. She knew I liked hearing everything she did.

"When I was getting back on my feet and didn't have a full-time job, I had to get out of my parents' house," she explained. "My ex and I had talked about moving in together, but we broke up shortly after. I needed a little financial boost.

"Long story short, I was talking to Melanie about it," she said, referring to her best friend, "and her younger sister Alison. Have you met Alison? I don't think you have. She is so gorgeous. Anyway, Alison suggested I find a sugar daddy. She had done it during college and said it was the best experience of her life. Money, travel, shopping. And all you had to do was go with older guys. I mean, obviously you know I have no problem with older men, so."

She stopped, wanting to give me a chance to catch up and ask questions. I just gazed at her. It was a non-judgmental, warm look with a slight smile.

"What I didn't realize was that Alison wasn't using some regular sugar baby website," Jess continued. "Initially she had just met a guy who got her into it, and she dated him and a few of his friends. But there was a kind of underground, Houston sugar website. Alison said otherwise you'd have to wade through a bunch of fakes.

"Alison referred me, and I signed up, and within a couple days I had meetings with a half-dozen potentials. And two weeks later? I had two arrangements and had moved out of my parents' house. I didn't realize until later that it's more common to have one arrangement at a time, but you know me. I'm anything but traditional." The words poured from her rapidly.

She looked at me, this time expecting a response. I honestly didn't know what to say. It didn't bother me. It didn't surprise me too much. That she wanted to do it more? It was a turn-on.

"Wow," I said. "That's a lot to take in. But obviously it worked out really well for you, it sounds like." I was searching for words to reassure her, as well as tease out the dirty details, which is what I really wanted.

"I don't think I knew what to expect," she said. "At first, meeting for coffee or a drink, it was just like real dating. But once I found a guy I was really attracted to, that's when I understood how much of an expectation the sex part was."

I smiled at her. "You were a whore," I said. My tone was one of appreciation.

Jess took the hint. She licked her lips. "I was," she said. "I had my job three days a week, and the other days I fucked my sugar daddies. I was such a whore for them."

"You know I want to hear all about them," I said. "I want every little detail. There is so much racing through my mind, I don't know where to ask you to begin. But maybe with this: how come you signed up again? And was it the same site?"

She nodded. "It was," she said. "I didn't want to waste my time."

"So you're serious about it," I observed.

"I think I am," she said. "Moving in with you is a big step. You know I don't like to be dependent on someone. This is a way to express a little independence." She looked intently at me. "Plus, I want the money. The money makes me so fucking wet."

"I have to admit, this is a bit of a surprise," I said. "But I am really hard right now. Why don't you tell me about one of them while we close out and head back to the room."

"Here's an easy one," she said. "The first arrangement was with an old oil and gas executive. I'll jump ahead a little bit, but this is a quick story. He had a friend who became my third sugar daddy. But all he ever wanted to do was take pictures of my feet. And jerk off on them. I learned really quickly that guys with fetishes like that are really common."

"I can't imagine paying a woman just to jerk off on her feet," I said. We started the walk back to our suite.

"He gave me a thousand dollars every time I saw him, too," she said.

"Jesus," I whistled.

"The oil and gas executive was my main daddy," she said matter-of-factly, revealing that she had gotten familiar with the lifestyle. I marveled that she could have kept it from me. "After our first couple meetings? He would just give me $3,000 on the first of every month, wired straight into my bank account. I think he had a self-confidence problem. He was polite and perfectly good looking, but he really couldn't believe I'd have sex with him. Or maybe he just didn't want to put in the effort it would take to get younger women to sleep with him. Whatever. The sex was vanilla. He was very into romance. I put on a show for the money. I realized I was good at it! I was very convincing. It became such a power trip."

We arrived back in the room, and I pushed Jess against the front door after it closed and kissed her urgently.

"I can't believe you could keep this from me for so long," I said, breathing rapidly. "It's so fucking hot."

She looked at me seriously. "Does it really turn you on?"

I took her hand and put it against my linen shorts, so she could feel my erection. "That answer the question?" I said.

"And if I do it again?" she asked.

"Just like in the past," I said. "You tell me every detail? I have no problem with it."

She smiled like she had just won something. "You're really going to love hearing about my third daddy. He was my favorite. I called him Dirty Daddy. Where's the blow?"